Ph 3P/I 2-Catalyzed beckmann rearrangement of ketoximes into amides

Synthetic Communications

Volumn 42, Issue 23, 2012, Pages 3532-3539

  Xu, Feng ^a   Wang, Ni Ge ^a   Tian, You Ping ^a   Chen, Yong Mei ^b   Liu, Wei Chun ^a  

^a SHAANXI NORMAL UNIVERSITY   (China)

^b XI'AN JIAOTONG UNIVERSITY   (China)

Author keywords

Amide; Beckman rearrangement; iodine; ketoximes; triphenylphosphine

Indexed keywords

ACETONITRILE; AMIDE; IODINE; OXIME DERIVATIVE; TRIPHENYLPHOSPHINE;

ARTICLE; BECKMANN REARRANGEMENT; CATALYSIS; REACTION ANALYSIS; TEMPERATURE;

EID: 84864663943     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397911.2011.585270     Document Type: Article

References (38)

1. Smith, M. B.; March, J. In Advanced Organic Chemistry, 5th ed.; John Wiley & Sons: New York, 2001; p. 1415. and references therein.
2. Xia, C. G.; Chen, J.; Xiao, L. F. p-Toluenesulfonic acid-mediated zinc chloride: Highly effective catalyst for the Beckmann rearrangement. Tetrahedron Lett. 2007, 48, 7218-7221. (Pubitemid 47361262)
3. Ghial, M.; Abbaspur, A.; Kalbasi, R. J. Vapor-phase Beckmann rearrangement of cyclohexanone oxime over H3PO4=ZrO2-TiO2. Appl. Catal. A 2005, 287, 83-88.
4. Formi, L.; Fornasari, G.; Giordano, G.; Lucarelli, C.; Katovic, A.; Trifiro, F.; Perri, C.; Nagy, J. B. Vapor-phase Beckmann rearrangement using high silica zeolite catalyst. Phys. Chem. Chem. Phys. 2004, 6, 1842-1847.
5. Mao, D.; Lu, G.; Chen, Q. 6-Aminocapronitrile as an alternative monomer for the nylon 6 synthesis. Appl. Catal. A: Gen. 2005, 279, 145-153.
6. Mao, D.; Chen, Q.; Lu, G. Vapor-phase Beckmann rearrangement of cyclohexanone oxime over B2O3=TiO2-ZrO2. Appl. Catal. A: Gen. 2003, 244, 273-282.
7. Chandrasekhar, S.; Gopalaiah, K. Ketones to amides via a formal Beckmann rearrangement in one pot: A solvent-free reaction promoted by anhydrous oxalic acid: Possible analogy with the Schmidt reaction. Tetrahedron Lett. 2003, 44, 7437-7439. (Pubitemid 37102973)
8. Chandrasekhar, S.; Gopalaiah, K. Beckmann reaction of oximes catalysed by chloral: Mild and neutral procedures. Tetrahedron Lett. 2003, 44, 755-756. (Pubitemid 36153242)
9. Khodaei, M. M.; Meybodi, F. A.; Rezai, N.; Salehi, P. Solvent-free Beckmann rearrangement of ketoximes by anhydrous ferric chloride. Synth. Commun. 2001, 31, 2047-2050. (Pubitemid 32718140)
10. Boero, M.; Ikeshoji, T.; Liew, C. C.; Terakura, K.; Parrinello, M. Hydrogen bond-driven chemical reactions: Beckmann rearrangement of cyclohexanone oxime into e-caprolactam in supercritical water. J. Am. Chem. Soc. 2004, 126, 6280-6286. (Pubitemid 38657055)
11. Ikushima, Y.; Hatakeda, K.; Sato, M.; Stao, O.; Arai, M. Innovation in a chemical reaction process using a supercritical water microreaction system: Environmentally friendly production of e-caprolactam. Chem. Commun. 2002, 19, 2208-2209. (Pubitemid 35155705)
12. Ikushima, Y.; Hatakeda, K.; Stao, O.; Yokoyama, T.; Arai, M. Noncatalytic organic synthesis using supercritical water: The peculiarity near the critical point. Angew. Chem. Int. Ed. 1999, 38, 2910-2914. (Pubitemid 29479964)
13. Ikushima, Y.; Stao, O.; Sato, M.; Hatakeda, K.; Arai, M. Innovations in chemical reaction processes using supercritical water: An environmental application to the production of e-caprolactam. Chem. Eng. Sci. 2003, 58, 935-941. (Pubitemid 36310128)
14. Futuya, Y.; Ishihara, K.; Yamamoto, H. Cyanuric chloride as a mild and active Beckmann rearrangement catalyst. J. Am. Chem. Soc. 2005, 127, 11240-11241. (Pubitemid 41176874)
15. Wang, B.; Gu, Y.; Luo, C.; Yang, T.; Yang, L.; Suo, J. Sulfamic acid as a cost-effective and recyclable catalyst for liquid Beckmann rearrangement, a green process to produce amides from ketoximes without waste. Tetrahedron Lett. 2004, 45, 3369-3372. (Pubitemid 38471613)
16. Li, D.; Shi, F.; Guo, S.; Deng, Y. Highly efficient Beckmann rearrangement and dehydration of oximes. Tetrahedron Lett. 2005, 46, 671-674. (Pubitemid 40037927)
17. Zhu, M.; Cha, C.; Deng, W.; Shi, X. A mild and efficient catalyst for the Beckmann rearrangement, BOP-Cl. Tetrahedron Lett. 2006, 47, 4861-4863. (Pubitemid 43831116)
18. Sardarian, A. R.; Shahsavari-Fard, Z.; Shahsavari, H. R.; Ebrahini, Z. A concise synthesis of 2,5-dideoxy-2,5-imino-D-mannitol (DMDP) and homo DMDP from L-xylose. Tetrahedron Lett. 2007, 48, 2369-2372.
19. Ramalingan, C.; Park, Y. T. Mercury-catalyzed rearrangement of ketoximes into amides and lactams in acetonitrile. J. Org. Chem. 2007, 72, 4536-4538. (Pubitemid 46903329)
20. Su, W. K.; Zhang, Y.; Li, J. J.; Li, P. A simple and efficient procedure for the Beckmann rearrangement of oxime using bis-(trichloromethyl) carbonate=DMF. Org. Prep. Proc. Int. 2008, 40, 543-550.
21. Pi, H. J.; Dong, J. D.; An, N.; Du, W.; Deng, W. P. Unexpected results from the re-investigation of the Beckmann rearrangement of ketoximes into amides by using TsCl. Tetrahedron 2009, 65, 7790-7793.
22. Ronchin, L.; Vavasori, A. On the mechanism of the organocatalyzed Beckmann rearrangement of cyclohexanone oxime by trifluoroacetic acid in aprotic solvent. J. Mol. Catal. A: Chem. 2009, 313, 22-30.
23. Ramalingan, C.; Park, Y. T. An efficient and versatile one-pot Beckmann rearrangement of ketoximes using mesitylenesulfonyl chloride. Synthesis 2008, 9, 1351-1358. (Pubitemid 351709850)
24. Yadav, L. D. S.; Srivastava, V. P. Bromodimethylsulfonium bromide (BDMS) in ionic liquid: A mild and efficient catalyst for Beckmann rearrangement. Tetrahedron Lett. 2010, 51, 739-743.
25. Ganguly, N. C.; Mondal, P. Efficient iodine-mediated Beckmann rearrangement of ketoximes to amides under mild neutral conditions. Synthesis 2011, 8.
26. Iranpoor, N.; Firouzabadi, H.; Aghapour, G. A rapid and facile conversion of primary amides and aldoximes to nitriles and ketoximes to amides with triphenylphosphine and N-chlorosuccinimide. Synth. Commun. 2002, 32, 2535-2541. (Pubitemid 34851685)
27. Tian, Y. P.; Xu, F.; Wang, Y.; Wang, J. J.; Li, H. L. PPh3-catalysed one-pot three-componment syntheses of a-aminophosphonates under solvent-free conditions. J. Chem. Res. 2009, 2, 78-80.
28. Sato, A.; Yorimitsu, H.; Oshima, K. Radical phosphination of organic halides and alkyl imidazole-1-carbothioates. J. Am. Chem. Soc. 2006, 128, 4240-4241.
29. Alizadeh, A.; Sheikhi, E. One-pot synthesis of functionalized hydantoin derivatives via a four-component reaction between an amine, an arylsulfonyl isocyanate, and an alkyl propiolate or dialkyl acetylene-dicarboxylate in the presence of triphenylphosphine. Tetrahedron Lett. 2007, 48, 4887-4890. (Pubitemid 46900952)
30. Yang, Y.; Shi, M. Ring-expanding reaction of cyclopropyl amides with triphenylphosphine and carbon tetrahalide. J. Org. Chem. 2005, 70, 8645-8648. (Pubitemid 41457043)
31. Lipshutz, B. H.; Chung, D. W.; Rich, B.; Corral, R. Simplification of the Mitsunobu reaction: Di-p-chlorobenzyl azodicarboxylate: A new azodicarboxylate. Org. Lett. 2006, 8, 5069-5072. (Pubitemid 44728880)
32. Anilkumar, G.; Nambu, H.; Kota, Y. A simple and efficient iodination of alcohols on polymer-supported triphenylphosphine. Org. Proc. Res. Dev. 2002, 6, 190-191.
33. Ponzo, V. L.; Bianchi, D. A.; Kaufman, T. S. Carbonyl transposition of a-hydroxyamidals mediated by triphenylphosphine-iodine: A new entry to tetrahydroisoquinolin-4-ones. Tetrahedron Lett. 1998, 39, 3409-3412. (Pubitemid 28218282)
34. Deng, W. P.; Du, W. T.; Pi, H. J.; Dong, J. D.; An, N. Unexpected results from the re-investigation of the Beckmann rearrangement of ketoximes into amides by using TsCl. Tetrahedron 2009, 65, 7790-7793.
35. Hashimoto, M.; Obora, Y.; Sakaguchi, S.; Ishii, Y. Beckmann rearrangement of ketoximes to lactams by triphosphazene catalyst. J. Org. Chem. 2008, 73, 2894-2897. (Pubitemid 351483004)
36. Sonawana, H. R.; Lanjundiah, B. S.; Kulkarni, D. G.; Ahuja, J. R. A unique 1,2-shift selectivity in 2-hydroxypropiophenone dimethylacetals: Generation of new methodologies for methyl-2-arylpropanoates and 1,2-carbonyl transposition. Tetrahedron 1988, 44, 7319-7324.
37. Barrillier, D.; Levillain, J.; Vazeux, M. Halides-based electrophiles-mediated epoxide ring-opening reactions of a,b-epoxysulfoxides in C6-series: Deoxygenation versus dehydration and an overall 1,2-keto transposition. Tetrahedron 1994, 50, 5413-5424.
38. BoJitt, V.; Mioskowski, C.; Lee, S. G.; Falck, J. R. Direct preparation of 2-deoxy-D-glucopyranosides from glucals without Ferrier rearrangement. J. Org. Chem. 1990, 55, 5812-5813.